Tocopherol derivatives and manufacture thereof



Patented June 10, 1941 TOCOIPHEROL DERIVATIVES AND MANU- FACTURE THEREOF Paul Kan-er, Zurich, Switzerland, assignor to HofEmann-La Roche Inc., Nutley, N. J., a corporation of New Jersey No Drawing. Applic'ation May 16, 1939, Serial No. 273,998. In Switzerland June 1, 1938 2 Claims. (Cl. 260-333) ble to introduce the alkylene group -CH=CR= CHR' into p-tocopherol. Thereby, this alkylene group probably enters the benzene nucleus, homologues of p-tocopherols being formed. The 01- ing at 70-80" 0. Then 4 parts by weight of anhydrous zinc chloride and 20 parts by weight of allyl bromide are added and the reaction mixture heated to boiling for 2 hours under a reflux condenser. During the reaction hydrogen bromide escapes. When the reaction has come to an end, the product is diluted with water, the aqueous layer separated from the petroleum ether layer, which is washed with water, and the solvent evaporated in vacuo. An oily residue remains which represents the condensation product from p-tocopherol and allyl bromide, the ally] p-tocopherol. The compound already reduces alcoholic silver nitrate solution at room temperalowing materials can be used as unsaturated alkyl 15 ture and has an absorption maximum at about halides: allyl bromide, phytyl bromide and the 293ILIL- like. For the purpose of bringing about the con- I claim:

densation, zinc chloride, aluminium chloride and the like can be employed.

The new compounds possess a stronger reducing action on neutral silver nitrate solution than p-tocopherol. They are to be used as medicinal preparations.

Example 4 parts by weight of p-tocopherol are dissolved in 80 parts by weight 01 anhydrous benzine boil- 1. Process for the manufacture of allyl-p-toco pherol, comprising reacting allyl halide with ptocopherol in the presence of an acid condensing agent. v

2. Allyl-p-tocopherol produced by condensing an allyl halide with p-tocopherol under acid conditions.

PAUL KARRER. 

